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US 6,143,569 AGranted
Chelators exhibiting triple fluorescence
AssigneeThe United States of America as represented by the Secretary of the Navy
InventorsGreg E. Collins, Ling-Siu Choi
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Abstract
A polyfunctional amine, such as cyclam, substituted with 4-(N,N-dimethylao) benzonitrile, exhibits triple fluorescence and complexes with metal ions. The complexation of metal ions with the fluorophore changes the triple fluorescence characteristics of the fluorophore. Thus, this substituted polyfunctional amine provides an effective indicator for the qualitative and quantitative detection of metals.
Claims20
A compound of the formula:
- ##STR3## wherein R.sup.1 is:
- a group having the formula:
- ##STR4## wherein R.sup.2 and R.sup.3 are unsubstituted C.sub.2 to C.sub.4 alkylene groups or C.sub.2 to C.sub.4 alkylene groups substituted with an aliphatic group, and may be the same as or different from one another;
- R.sup.4 is -, an unsubstituted C.sub.2 to C.sub.4 alkene group, or a C.sub.2 to C.sub.4 alkylene group substituted with an aliphatic group, and may be the same or different from any other R.sup.4 groups present and may be the same or different from R.sup.2 and R.sup.3 ;
- Q is NH, NR.sup.7, or O, and may be the same as or different from any other Q group present;
- R.sup.5, R.sup.6, and R.sup.7 are aliphatic groups and may be the same as or different from each other, and
- y is an integer having a value of from 1 to 5;
- or
- an azacyclo group having at least two ring nitrogens, at least one of said ring nitrogens being substituted by said benzonitrile group and at least one of said ring nitrogens being 2 to 4 carbon atoms from said benzonitrile-substituted ring nitrogen, said azacyclo group having as ring members at least one additional heteroatom selected from the group consisting of N, O, and S, said at least one additional heteroatom having at least 2 carbons between it and the nearest of other ring member heteroatoms;
- and
- R.sup.9, R.sup.10, R.sup.11, and R.sup.12 are H or CH.sub.3 and may be the same as or different from each other;
- wherein said compound exhibits fluorescent emission at a first set of three separate emission bands in response to a light at an excitation wavelength in the absence of a metal ion and at a second set of three separate emission bands in the presence of said metal ion, the difference between said first and second set of three separate emission bands being characteristic of said metal ion.
9 more elements
A method of detecting a metal ion in a liquid, comprising the steps of:
- adding a compound of the formula:
- ##STR7## wherein R.sup.1 is:
- a group having the formula:
- ##STR8## wherein R.sup.2 and R.sup.3 are unsubstituted C.sub.2 to C.sub.4 alkylene groups or C.sub.2 to C.sub.4 alkylene groups substituted with an aliphatic group, and may be the same as or different from one another;
- R.sup.4 is -, an unsubstituted C.sub.2 to C.sub.4 alkylene group, or a C.sub.2 to C.sub.4 alkylene group substituted with an aliphatic group, and may be the same or different from any other R.sup.4 groups present and may be the same or different from R.sup.2 and R.sup.3 ;
- Q is NH, NR.sup.7, or O, and may be the same as or different from any other Q group present;
- R.sup.5, R.sup.6, and R.sup.7 are aliphatic groups and may be the same as or different from each other;
- and
- y is an integer having a value of from 1 to 5;
- or
- an azacyclo group having at least two ring nitrogens, at least one of said ring nitrogens being substituted by said benzonitrile group and at least one of said ring nitrogens being 2 to 4 carbon atoms from said benzonitrile-substituted ring nitrogen, said azacyclo group having as ring members at least one additional heteroatom selected from the group consisting of N, O, and S, said at least one additional heteroatom having at least 2 carbons between it and the nearest of other ring member heteroatoms;
- and
- R.sup.9, R.sup.10, R.sup.11, and R.sup.12 are H or CH.sub.3 and may be the same as or different from each other, to said liquid, wherein said compound exhibits fluorescent emission at a first set of three separate emission frequencies in response to a light at an excitation wavelength in the absence of said metal ion and at a second set of three separate emission bands in the presence of said metal ion, said first and second set of three separate emission frequencies being the same as or different from each other and wherein the difference between said first and second set of three separate emission bands is characteristic of said metal ion;
- exposing said liquid including said compound to said light at said excitation wavelength;
- detecting said fluorescent emission at least at one of said second three separate emission bands;
- comparing said detecting fluorescent emission with a standard, whereby the presence of said metal ion is determined.
13 more elements
Dependencies are inferred from the claim text.